Active compound combinations having insecticidal and acaricidal properties

ABSTRACT

The invention relates to novel insecticidal active compound combinations comprising, firstly, cyclic ketoenols or other insecticidally active compounds and, secondly, further insecticidally active compounds from the group of the anthranilamides, which combinations are highly suitable for controlling animal pests, such as insects and unwanted acarides.

This application is a 35 U.S.C. §371 U.S. National Phase filing of International Application No. PCT/EP2004/013198, filed Nov. 20, 2004, which claims the benefit of German Patent Application No. 103 56 551.5, filed Dec. 4, 2003 and German Patent Application No. 10 2004 021 566.9, filed May 3, 2004.

The present invention relates to novel active compound combinations comprising, firstly, known cyclic ketoenols and, secondly, further known insecticidally active compounds which combinations are highly suitable for controlling animal pests, such as insects and unwanted acarides.

It is already known that certain cyclic ketoenols have herbicidal, insecticidal and acaricidal properties. The activity of these compounds is good; however, at low application rates it is sometimes unsatisfactory.

Unsubstituted bicyclic 3-arylpyrrolidine-2,4-dione derivatives (EP-A 0 355 599 and EP-A 0 415 211) and substituted monocyclic 3-arylpyrrolidine-2,4-dione derivatives (EP-A 0 377 893 and EP-A 0 442 077) having herbicidal, insecticidal or acaricidal action are known.

Also known are polycyclic 3-arylpyrrolidine-2,4-dione derivatives (EP-A 0 442 073) and 1H-arylpyrrolidinedione derivatives (EP-A 0 456 063, EP-A 0 521 334, EP-A 0 596 298, EP-A 0 613 884, EP-A 0 613 885, WO 94/01 997, WO 95/26 954, WO 95/20 572, EP-A 0 668 267, WO 96/25395, WO 96/35664, WO 97/01535, WO 97/02243, WO 97/36868, WO 97/43275, WO 98/05638, WO 98/06721, WO 98/25928, WO 99/16748, WO 99/24437, WO 99/43649, WO 99/48869 and WO 99/55673, WO 01/23354, WO 01/74770). The activity of these compounds is good; however, at low application rates it is sometimes unsatisfactory.

It is also known that mixtures of phthalamides and further bioactive compounds have insecticidal and/or acaricidal action (WO 02/087334). However, the activity of this mixture is not always optimal.

Furthermore, it is already know that numerous heterocycles, organotin compounds, benzoylureas and pyrethroids have insecticidal and acaricidal properties (cf. WO 93/22297, WO 93/10083, DE-A 26 41 343, EP-A 0 347 488, EP-A 210 487, U.S. Pat. No. 3,364,177 and EP-A 234 045). However, the activity of these compounds is likewise not always satisfactory.

It has now been found that mixtures of compounds of the formula (I) (group 1)

in which

-   X represents halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano, -   W¹, Y and Z independently of one another represent hydrogen,     halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano, -   A³ represents hydrogen, in each case optionally halogen-substituted     alkyl, alkoxyalkyl, saturated, optionally substituted cycloalkyl in     which optionally at least one ring atom is replaced by a heteroatom, -   A⁴ represents hydrogen or alkyl, -   A³ and A⁴ furthermore together with the carbon atom to which they     are attached represent a saturated or unsaturated, unsubstituted or     substituted cycle which optionally contains at least one heteroatom, -   D represents hydrogen or an optionally substituted radical from the     group consisting of alkyl, alkenyl, alkoxyalkyl, saturated     cycloalkyl in which optionally one or more ring members are replaced     by heteroatoms, -   A³ and D together with the atoms to which they are attached     represent a saturated or unsaturated cycle which is unsubstituted or     substituted in the A³, D moiety and optionally contains at least one     heteroatom, -   G¹ represents hydrogen (a) or represents one of the groups

-   E represents a metal ion or an ammonium ion, -   L¹ represents oxygen or sulfur, -   M¹ represents oxygen or sulfur, -   R²⁰ represents in each case optionally halogen-substituted alkyl,     alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or optionally     halogen-, alkyl- or alkoxy-substituted cycloalkyl which may be     interrupted by at least one heteroatom, in each case optionally     substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or     hetaryloxyalkyl, -   R²¹ represents in each case optionally halogen-substituted alkyl,     alkenyl, alkoxyalkyl, polyalkoxyalkyl or represents in each case     optionally substituted cycloalkyl, phenyl or benzyl, -   R²² represents optionally halogen-substituted alkyl or optionally     substituted phenyl, -   R²³ and R²⁴ independently of one another represent in each case     optionally halogen-substituted alkyl, alkoxy, alkylamino,     dialkylamino, alkylthio, alkenylthio, cycloalkylthio or represent in     each case optionally substituted phenyl, benzyl, phenoxy or     phenylthio and -   R²⁵ and R²⁶ independently of one another represent hydrogen, in each     case optionally halogen-substituted alkyl, cycloalkyl, alkenyl,     alkoxy, alkoxyalkyl, represent optionally substituted phenyl,     represent optionally substituted benzyl or together with the     nitrogen atom to which they are attached represent an optionally     substituted ring which is optionally interrupted by oxygen or     sulfur,     or an insecticidally active compound (group 2), preferably -   (2-1) amitraz (known from DE-A 20 61 132)

and/or

-   (2-2) buprofezin (known from DE-A 28 24 126)

and/or

-   (2-3) triazamate (known from EP-A0 213 718)

and/or

-   (2-4) pymetrozine (known from EP-A 0 314 615)

and/or

-   (2-5) pyriproxifen (known from EP-A 0 128 648)

and/or

-   (2-6) flonicamid (known from EP-A 0 580 374)

and/or

-   (2-7) pirimicarb (known from GB 1 181 657)

and at least one active compound from the group of the anthranilamides of the formula (II) are synergistically effective and have very good insecticidal and acaricidal properties.

Surprisingly, the insecticidal and/or acaricidal activity of the active compound combinations according to the invention is higher than the sum of the activities of the individual active compounds. Thus, an unforeseeable true synergistic effect is present, and not just an addition of activities. In addition to at least one active compound of the formula (I) or one active compound of group 2 (compounds (2-1) to (2-7)), the active compound combinations according to the invention comprise at least one active compound of the formula (II).

Preference is given to active compound combinations comprising compounds of the formula (I) in which

-   W¹ represents hydrogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, chlorine, bromine     or fluorine, -   X represents C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl, fluorine,     chlorine or bromine, -   Y and Z independently of one another represent hydrogen,     C₁-C₄-alkyl, halogen, C₁-C₄-alkoxy or C₁-C₄-haloalkyl, -   A³ represents hydrogen or in each case optionally     halogen-substituted C₁-C₆-alkyl or C₃-C₈-cycloalkyl, -   A⁴ represents hydrogen, methyl or ethyl, -   A³ and A⁴ furthermore together with the carbon atom to which they     are attached represent saturated C₃-C₆-cycloalkyl in which     optionally one ring member is replaced by oxygen or sulfur and which     is optionally mono- or disubstituted by C₁-C₄-alkyl, trifluoromethyl     or C₁-C₄-alkoxy, -   D represents hydrogen, in each case optionally fluorine- or     chlorine-substituted C₁-C₆-alkyl, C₃-C₄-alkenyl or C₃-C₆-cycloalkyl, -   A³ and D together represent optionally methyl-substituted     C₃-C₄-alkanediyl in which optionally one methylene group is replaced     by sulfur, -   G¹ represents hydrogen (a) or represents one of the groups

-   E represents a metal ion or an ammonium ion, -   L¹ represents oxygen or sulfur, -   M¹ represents oxygen or sulfur, -   R²⁰ represents in each case optionally halogen-substituted     C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,     C₁-C₄-alkylthio-C₁-C₄-alkyl or optionally fluorine-, chlorine-,     C₁-C₄-alkyl- or C₁-C₂-alkoxy-substituted C₃-C₆-cycloalkyl, -    represents optionally fluorine-, chlorine-, bromine-, cyano-,     nitro-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, trifluoromethyl- or     trifluoromethoxy-substituted phenyl, -    represents in each case optionally chlorine- or methyl-substituted     pyridyl or thienyl, -   R²¹ represents in each case optionally fluorine- or     chlorine-substituted C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl,     C₁-C₄-alkoxy-C₂-C₄-alkyl, -    represents optionally methyl- or methoxy-substituted     C₅-C₆-cycloalkyl or -    represents in each case optionally fluorine-, chlorine-, bromine-,     cyano-, nitro-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, trifluoromethyl- or     trifluoromethoxy-substituted phenyl or benzyl, -   R²² represents optionally fluorine-substituted C₁-C₄-alkyl or     represents optionally fluorine-, chlorine-, bromine-, C₁-C₄-alkyl-,     C₁-C₄-alkoxy-, trifluoromethyl-, trifluoromethoxy-, cyano- or     nitro-substituted phenyl, -   R²³ represents in each case optionally fluorine- or     chlorine-substituted C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylamino,     C₁-C₄-alkylthio or represents in each case optionally fluorine-,     chlorine-, bromine-, nitro-, cyano-, C₁-C₄-alkoxy-,     trifluoromethoxy-, C₁-C₄-alkylthio-, C₁-C₄-haloalkylthio-,     C₁-C₄-alkyl- or trifluoromethyl-substituted phenyl, phenoxy or     phenylthio, -   R²⁴ represents C₁-C₄-alkoxy or C₁-C₄-alkylthio, -   R²⁵ represents C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy,     C₃-C₆-alkenyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, -   R²⁶ represents C₁-C₆-alkyl, C₃-C₆-alkenyl or     C₁-C₄-alkoxy-C₁-C₄-alkyl, -   R²⁵ and R²⁶ furthermore together represent an optionally methyl- or     ethyl-substituted C₃-C₆-alkylene radical in which optionally one     carbon atom is replaced by oxygen or sulfur,     and at least one active compound of the formula (II).

In the halogen radicals in the preferred ranges, halogen preferably represents chlorine and fluorine.

Particular preference is given to active compound combinations comprising compounds of the formula (I) in which

-   W¹ represents hydrogen, methyl, ethyl, chlorine, bromine or methoxy, -   X represents chlorine, bromine, methyl, ethyl, propyl, isopropyl,     methoxy, ethoxy or trifluoromethyl, -   Y and Z independently of one another represent hydrogen, fluorine,     chlorine, bromine, methyl, ethyl, propyl, isopropyl, trifluoromethyl     or methoxy, -   A³ represents methyl, ethyl, propyl, isopropyl, butyl, isobutyl,     sec-butyl, tert-butyl, cyclopropyl, cyclopentyl or cyclohexyl, -   A⁴ represents hydrogen, methyl or ethyl, -   A³ and A⁴ furthermore together with the carbon atom to which they     are attached represent saturated C₆-cycloalkyl in which optionally     one ring member is replaced by oxygen and which is optionally     monosubstituted by methyl, ethyl, methoxy, ethoxy, propoxy or     butoxy, -   D represents hydrogen, represents methyl, ethyl, propyl, isopropyl,     butyl, isobutyl, allyl, cyclopropyl, cyclopentyl or cyclohexyl, -   A³ and D together represent optionally methyl-substituted     C₃-C₄-alkanediyl, -   G¹ represents hydrogen (a) or represents one of the groups

-   L¹ represents oxygen or sulfur, -   M¹ represents oxygen or sulfur, -   R²⁰ represents C₁-C₈-alkyl, C₂-C₄-alkenyl, methoxymethyl,     ethoxymethyl, ethylthiomethyl, cyclopropyl, cyclopentyl or     cyclohexyl, -    represents phenyl which is optionally mono- to disubstituted by     fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy,     trifluoromethyl or trifluoromethoxy, -    represents pyridyl or thienyl, each of which is optionally mono- to     disubstituted by chlorine or methyl, -   R²¹ represents C₁-C₈-alkyl, C₂-C₄-alkenyl, methoxyethyl, ethoxyethyl     or represents phenyl or benzyl, -   R²⁵ and R²⁶ independently of one another represent methyl, ethyl or     together with the nitrogen atom to which they are attached represent     morpholino,     and at least one active compound of the formula (II).

Very particular preference is given to active compound combinations comprising compounds of the formula (I) in which

-   W¹ represents hydrogen or methyl, -   X represents chlorine, bromine or methyl, -   Y and Z independently of one another represent hydrogen, chlorine,     bromine or methyl, -   A³ and A⁴ furthermore together with the carbon atom to which they     are attached represent saturated C₆-cycloalkyl in which optionally     one ring member is replaced by oxygen and is optionally     monosubstituted by methyl, methoxy, ethoxy, propoxy or butoxy, -   D represents hydrogen, -   G¹ represents hydrogen (a) or represents one of the groups

-   L¹ represents oxygen or sulfur, -   M¹ represents oxygen or sulfur, -   R²⁰ represents C₁-C₈-alkyl, C₂-C₄-alkenyl, methoxymethyl,     ethoxymethyl, ethylmethylthio, cyclopropyl, cyclopentyl, cyclohexyl, -    represents phenyl which is optionally monosubstituted by fluorine,     chlorine, bromine, methyl, methoxy, trifluoromethyl,     trifluoromethoxy, cyano or nitro, -    represents pyridyl or thienyl, each of which is optionally     monosubstituted by chlorine or methyl, -   R²¹ represents C₁-C₈-alkyl, C₂-C₄-alkenyl, methoxyethyl,     ethoxyethyl, phenyl or benzyl, -   R²⁵ and R²⁶ independently of one another represent methyl, ethyl or     together with the nitrogen atom to which they are attached represent     morpholino,     and at least one active compound of the formula (II).

Especially preferred are active compound combinations comprising at least one of the following compounds of the formula (I-a)

(I-a)

Example No. W¹ X Y Z R²⁷ G¹ m.p. (° C.) I-a-1 H Br 5-CH₃ H OCH₃ CO-i-C₃H₇ 122 I-a-2 H Br 5-CH₃ H OCH₃ CO₂—C₂H₅ 140-142 I-a-3 H CH₃ 5-CH₃ H OCH₃ H >220   I-a-4 H CH₃ 5-CH₃ H OCH₃ CO₂—C₂H₅ 128 I-a-5 CH₃ CH₃ 3-Br H OCH₃ H >220   I-a-6 CH₃ CH₃ 3-Cl H OCH₃ H 219 I-a-7 H Br 4-CH₃ 5-CH₃ OCH₃ CO-i-C₃H₇ 217 I-a-8 H CH₃ 4-Cl 5-CH₃ OCH₃ CO₂C₂H₅ 162 I-a-9 H CH₃ 4-CH₃ 5-CH₃ OCH₃

oil I-a-10 CH₃ CH₃ 3-CH₃ 4-CH₃ OCH₃ H >220   I-a-11 H CH₃ 5-CH₃ H OC₂H₅

oil I-a-12 CH₃ CH₃ 3-Br H OC₂H₅ CO-i-C₃H₇ 212-214 I-a-13 H CH₃ 4-CH₃ 5-CH₃ OC₂H₅ CO-n-Pr 134 I-a-14 H CH₃ 4-CH₃ 5-CH₃ OC₂H₅ CO-i-Pr 108 I-a-15 H CH₃ 4-CH₃ 5-CH₃ OC₂H₅ CO-c-Pr 163 and at least one active compound of the formula (II).

Especially preferred are active compound combinations comprising the compound of the formula (I-a-4)

and at least one active compound of the formula (II).

Depending inter alia on the nature of the substituents, the compounds of the formula (I) can be present as geometrical and/or optical isomers or isomer mixtures of varying composition which, if desired, may be separated in a customary manner. The present invention provides both the pure isomers and the isomer mixtures, their preparation and use and also compositions comprising them. However, hereinbelow, for the sake of simplicity, only compounds of the formula (I) are referred to, although what is meant are both pure compounds and, if appropriate, also mixtures having varying proportions of isomeric compounds.

Especially preferred are active compound combinations comprising a compound selected from the compounds (2-1) to (2-7) of group 2 and at least one active compound of the formula (II).

The anthranilamides of the formula (II) are likewise known compounds which are known from the following publications or embraced by them:

-   WO 01/70671, WO 03/015518, WO 03/015519, WO 03/016284, WO 03/016282,     WO 03/016283, WO 03/024222, WO 03/062226.

The generic formulae and definitions described in these publications and the individual compounds described therein are expressly incorporated herein by way of reference.

The anthranilamides can be summarized by the formula (II):

in which

-   A¹ and A² independently of one another represent oxygen or sulfur, -   X¹ represents N or CR¹⁰, -   R¹ represents hydrogen or represents C₁-C₆-alkyl, C₂-C₆-alkenyl,     C₂-C₆-alkynyl or C₃-C₆-cycloalkyl, each of which is optionally mono-     or polysubstituted, where the substituents independently of one     another may be selected from the group consisting of R⁶, halogen,     cyano, nitro, hydroxyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio,     C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₂-C₄-alkoxycarbonyl,     C₁-C₄-alkylamino, C₂-C₈-dialkylamino, C₃-C₆-cycloalkylamino,     (C₁-C₄-alkyl)-C₃-C₆-cycloalkylamino and R¹¹, -   R² represents hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,     C₃-C₆-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-alkylamino,     C₂-C₈-dialkylamino, C₃-C₆-cycloalkylamino, C₂-C₆-alkoxycarbonyl or     C₂-C₆-alkylcarbonyl, -   R³ represents hydrogen, R¹¹ or represents C₁-C₆-alkyl,     C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, each of which is     optionally mono- or polysubstituted, where the substituents     independently of one another may be selected from the group     consisting of R⁶, halogen, cyano, nitro, hydroxyl, C₁-C₄-alkoxy,     C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl,     C₁-C₄-alkylsulfonyl, C₂-C₆-alkoxycarbonyl, C₂-C₆-alkylcarbonyl,     C₃-C₆-trialkylsilyl, R¹¹, phenyl, phenoxy and a 5- or 6-membered     heteroaromatic ring, where each phenyl, phenoxy and 5- or 6-membered     heteroaromatic ring may optionally be substituted and where the     substituents independently of one another may be selected from one     to three radicals W or one or more radicals R¹², or -   R² and R³ may be attached to one another and form the ring M, -   R⁴ represents hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,     C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl,     C₂-C₆-haloalkynyl, C₃-C₆-halocycloalkyl, halogen, cyano, nitro,     hydroxyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio;     C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylthio,     C₁-C₄-haloalkylsulfinyl, C₁-C₄-haloalkylsulfonyl, C₁-C₄-alkylamino,     C₂-C₈-dialkylamino, C₃-C₆-cycloalkylamino, C₃-C₆-trialkylsilyl or     represents phenyl, benzyl or phenoxy, each of which is optionally     mono- or polysubstituted, where the substituents independently of     one another may be selected from the group consisting of     C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl,     C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl, C₂-C₄-haloalkynyl,     C₃-C₆-halocycloalkyl, halogen, cyano, nitro, C₁-C₄-alkoxy,     C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl,     C₁-C₄-alkylsulfonyl, C₁-C₄-alkylamino, C₂-C₈-dialkylamino,     C₃-C₆-cycloalkylamino, C₃-C₆-(alkyl)cycloalkylamino,     C₂-C₄-alkylcarbonyl, C₂-C₆-alkoxycarbonyl, C₂-C₆-alkylaminocarbonyl,     C₃-C₈-dialkylaminocarbonyl and C₃-C₆-trialkylsilyl, -   R⁵ and R⁸ in each case independently of one another represent     hydrogen, halogen or represent in each case optionally substituted     C₁-C₄-alkyl, C₁-C₄-haloalkyl, R¹², G, J, —OJ, —OG, —S(O)_(p)-J,     —S(O)_(p)-G, —S(O)_(p)-phenyl, where the substituents independently     of one another may be selected from one to three radicals W or from     the group consisting of R¹², C₁-C₁₀-alkyl, C₂-C₆-alkenyl,     C₂-C₆-alkynyl, C₁-C₄-alkoxy and C₁-C₄-alkylthio, where each     substituent may be substituted by one or more substituents     independently of one another selected from the group consisting of     G, J, R⁶, halogen, cyano, nitro, amino, hydroxyl, C₁-C₄-alkoxy,     C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl,     C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulfinyl,     C₁-C₄-haloalkylsulfonyl, C₁-C₄-alkylamino, C₂-C₈-dialkylamino,     C₃-C₆-trialkylsilyl, phenyl and phenoxy, where each phenyl or     phenoxy ring may optionally be substituted and where the     substituents independently of one another may be selected from one     to three radicals W or one or more radicals R¹², -   G in each case independently of one another represent a 5- or     6-membered non-aromatic carbocyclic or heterocyclic ring which may     optionally contain one or two ring members from the group consisting     of C(═O), SO and S(═O)₂ and which may optionally be substituted by     one to four substituents independently of one another selected from     the group consisting of C₁-C₂-alkyl, halogen, cyano, nitro and     C₁-C₂-alkoxy, or independently of one another represent     C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₇-cycloalkyl,     (cyano)-C₃-C₇-cycloalkyl, (C₁-C₄-alkyl)-C₃-C₆-cycloalkyl,     (C₃-C₆-cycloalkyl)-C₁-C₄-alkyl, where each cycloalkyl,     (alkyl)cycloalkyl and (cycloalkyl)alkyl may optionally be     substituted by one or more halogen atoms, -   J in each case independently of one another represent an optionally     substituted 5- or 6-membered heteroaromatic ring, where the     substituents independently of one another may be selected from one     to three radicals W or one or more radicals R¹², -   R⁶ independently of one another represent —C(=E¹)R¹⁹, LC(=E¹)R¹⁹,     —C(=E¹)LR¹⁹, -LC(=E¹)LR¹⁹, —OP(=Q)(OR¹⁹)₂, —SO₂LR¹⁸ or -LSO₂LR¹⁹,     where each E¹ independently of one another represents O, S, N—R¹⁵,     N—OR¹⁵, N—N(R¹⁵)₂, N—S═O, N—CN or N—NO₂, -   R⁷ represents hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, halogen,     C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,     C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylthio;     C₁-C₄-haloalkylsulfinyl, C₁-C₄-haloalkylsulfonyl, -   R⁹ represents C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy,     C₁-C₄-haloalkylsulfinyl or halogen, -   R¹⁰ represents hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, halogen,     cyano or C₁-C₄-haloalkoxy, -   R¹¹ in each case independently of one another represents in each     case optionally mono- to trisubstituted C₁-C₆-alkylthio,     C₁-C₆-alkylsulfenyl, C₁-C₆-haloalkylthio, C₁-C₆-haloalkylsulfenyl,     phenylthio or phenylsulfenyl, where the substituents independently     of one another may be selected from the list W, —S(O)_(n)N(R¹⁶)₂,     —C(=Q)R¹³, -L(C═O)R¹⁴, —S(C═O)LR¹⁴, —C(═O)LR¹³,     —S(O)_(n)NR¹³C(═O)R¹³, —S(O)_(n)NR¹³C(═O))LR¹⁴ or     —S(O)_(n)NR¹³S(O)₂LR¹⁴, -   L in each case independently of one another represents O, NR¹⁸ or S, -   R¹² in each case independently of one another represents —B(OR¹⁷)₂,     amino, SH, thiocyanato, C₃-C₈-trialkylsilyloxy, C₁-C₄-alkyl     disulfide, —SF₅, —C(=E¹)R¹⁹, -LC(=E¹)R¹⁹, —C(=E¹)LR¹⁹, -LC(=E¹)LR¹⁹,     —OP(=Q)(OR¹⁹)₂, —SO₂LR¹⁹ or -LSO₂LR¹⁹, -   Q represents O or S, -   R¹³ in each case independently of one another represent hydrogen or     represent in each case optionally mono- or polysubstituted     C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl or C₃-C₆-cycloalkyl, where     the substituents independently of one another may be selected from     the group consisting of R⁶, halogen, cyano, nitro, hydroxyl,     C₁-C₄-alkoxy, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl,     C₁-C₄-alkylamino, C₂-C₈-alkylamino, C₃-C₆-cycloalkylamino or     (C₁-C₄-alkyl)-C₃-C₆-cycloalkylamino, -   R¹⁴ in each case independently of one another represent in each case     optionally mono- or polysubstituted C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl,     C₂-C₂₀-alkynyl or C₃-C₆-cycloalkyl, where the substituents     independently of one another may be selected from the group     consisting of R⁶, halogen, cyano, nitro, hydroxyl, C₁-C₄-alkoxy,     C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-alkylamino,     C₂-C₈-dialkylamino, C₃-C₆-cycloalkylamino and     (C₁-C₄-alkyl)-C₃-C₆-cycloalkylamino or represent optionally     substituted phenyl, where the substituents independently of one     another may be selected from one to three radicals W or one or more     radicals R¹², -   R¹⁵ in each case independently of one another represent hydrogen or     represent in each case optionally mono- or polysubstituted     C₁-C₆-haloalkyl or C₁-C₆-alkyl, where the substituents independently     of one another may be selected from the group consisting of cyano,     nitro, hydroxyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,     C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylthio,     C₁-C₄-haloalkylsulfinyl, C₁-C₄-haloalkylsulfonyl, C₁-C₄-alkylamino,     C₂-C₈-dialkylamino, C₂-C₆-alkoxycarbonyl, C₂-C₆-alkylcarbonyl,     C₃-C₆-trialkylsilyl and optionally substituted phenyl, where the     substituents independently of one another may be selected from one     to three radicals W or one or more radicals R¹², or N(R¹⁵)₂     represents a cycle which forms the ring M, -   R¹⁶ represents C₁-C₁₂-alkyl or C₁-C₁₂-haloalkyl, or N(R¹⁶)₂     represents a cycle which forms the ring M, -   R¹⁷ in each case independently of one another represent hydrogen or     C₁-C₄-alkyl, or B(OR¹⁷)₂ represents a ring in which the two oxygen     atoms are attached via a chain having two to three carbon atoms     which are optionally substituted by one or two substituents     independently of one another selected from the group consisting of     methyl and C₂-C₆-alkoxycarbonyl, -   R¹⁸ in each case independently of one another represent hydrogen,     C₁-C₆-alkyl or C₁-C₆-haloalkyl, or N(R¹³)(R¹⁸) represents a cycle     which forms the ring M, -   R¹⁹ in each case independently of one another represent hydrogen or     represent in each case optionally mono- or polysubstituted     C₁-C₆-alkyl, where the substituents independently of one another may     be selected from the group consisting of cyano, nitro, hydroxyl,     C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,     C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylthio,     C₁-C₄-haloalkylsulfinyl, C₁-C₄-haloalkylsulfonyl, C₁-C₄-alkylamino,     C₂-C₈-dialkylamino, CO₂H, C₂-C₆-alkoxycarbonyl, C₂-C₆-alkylcarbonyl,     C₃-C₆-trialkylsilyl and optionally substituted phenyl, where the     substituents independently of one another may be selected from one     to three radicals W, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl or phenyl or     pyridyl, each of which is optionally mono- to trisubstituted by W, -   M in each case represents an optionally mono- to tetrasubstituted     ring which, in addition to the nitrogen atom attached to the     substituent pair R¹³ and R¹⁸, (R¹⁵)₂ or (R¹⁶)₂, contains two to six     carbon atoms and optionally additionally a further nitrogen, sulfur     or oxygen atom, where the substituents independently of one another     may be selected from the group consisting of C₁-C₂-alkyl, halogen,     cyano, nitro and C₁-C₂-alkoxy, -   W in each case independently of one another represent C₁-C₄-alkyl,     C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl,     C₂-C₄-haloalkenyl, C₂-C₄-haloalkynyl, C₃-C₆-halocycloalkyl, halogen,     cyano, nitro, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,     C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-alkylamino,     C₂-C₈-dialkylamino, C₃-C₆-cycloalkylamino,     (C₁-C₄-alkyl)-C₃-C₆-cycloalkylamino, C₂-C₄-alkylcarbonyl,     C₂-C₆-alkoxycarbonyl, CO₂H, C₂-C₆-alkylaminocarbonyl,     C₃-C₈-dialkylaminocarbonyl or C₃-C₆-trialkylsilyl, -   n in each case independently of one another represent 0 or 1, -   p in each case independently of one another represent 0, 1 or 2,     where, if (a) R⁵ represents hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,     C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₁-C₄-haloalkoxy,     C₁-C₄-haloalkylthio or halogen and (b) R⁸ represents hydrogen,     C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,     C₁-C₄-haloalkoxy, C₁-C₄-haloalkylthio, halogen, C₂-C₄-alkylcarbonyl,     C₂-C₆-alkoxycarbonyl, C₂-C₆-alkylaminocarbonyl or C₃-C₈     dialkylaminocarbonyl, (c) at least one substituent selected from the     group consisting of R⁶, R¹¹ and R¹² is present and (d) if R¹² is not     present, at least one of the radicals R⁶ and R¹¹ is different from     C₂-C₆-alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆-alkylaminocarbonyl     and C₃-C₈-dialkylaminocarbonyl.

The compounds of the general formula (II) comprise N-oxides and salts.

Depending inter alia on the nature of the substituents, the compounds of the formula (II) can be present as geometrical and/or optical isomers or isomer mixtures of varying composition which, if desired, may be separated in a customary manner. The present invention provides both the pure isomers and the isomer mixtures, their preparation and use and also compositions comprising them. However, hereinbelow, for the sake of simplicity, only compounds of the formula (II) are referred to, although what is meant are both pure compounds and, if appropriate, also mixtures having varying proportions of isomeric compounds.

Preference is given to active compound combinations comprising compounds of the formula (II-1)

in which

-   R² represents hydrogen or C₁-C₆-alkyl, -   R³ represents C₁-C₆-alkyl which is optionally substituted by one R⁶, -   R⁴ represents C₁-C₄-alkyl, C₁-C₂-haloalkyl, C₁-C₂-haloalkoxy or     halogen, -   R⁵ represents hydrogen, C₁-C₄-alkyl, C₁-C₂-haloalkyl,     C₁-C₂-haloalkoxy or halogen, -   R⁶ represents. —C(=E²)R¹⁹, -LC(=E²)R¹⁹, —C(=E²)LR¹⁹ or -LC(=E²)LR¹⁹,     where each E² independently of one another represents O, S, N—R¹⁵,     N—OR¹⁵, N—N(R¹⁵)₂, and each L independently of one another     represents O or NR¹⁸, -   R⁷ represents C₁-C₄-haloalkyl or halogen, -   R⁹ represents C₁-C₂-haloalkyl, C₁-C₂-haloalkoxy,     S(O)_(p)—C₁-C₂-haloalkyl or halogen, -   R¹⁵ in each case independently of one another represent hydrogen or     represent in each case optionally substituted C₁-C₆-haloalkyl or     C₁-C₆-alkyl, where the substituents independently of one another may     be selected from the group consisting of cyano, C₁-C₄-alkoxy,     C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl,     C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulfinyl     and C₁-C₄-haloalkylsulfonyl, -   R¹⁸ in each case represents hydrogen or C₁-C₄-alkyl, -   R¹⁹ in each case independently of one another represent hydrogen or     C₁-C₆-alkyl, -   p independently of one another represent 0, 1, 2.

In the radical definitions mentioned as being preferred, halogen represents fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.

Particular preference is given to active compound combinations comprising compounds of the formula (II-1) in which

-   R² represents hydrogen or methyl, -   R³ represents C₁-C₄-alkyl (in particular methyl, ethyl, n-,     isopropyl, n-, iso-, sec-, tert-butyl), -   R⁴ represents methyl, trifluoromethyl, trifluoromethoxy, fluorine,     chlorine, bromine or iodine, -   R⁵ represents hydrogen, fluorine, chlorine, bromine, iodine,     trifluoromethyl or trifluoroethoxy, -   R⁷ represents chlorine or bromine, -   R⁹ represents trifluoromethyl, chlorine, bromine, difluoromethoxy or     trifluoroethoxy.

Very particular preference is given to active compound combinations comprising the following compounds of the formula (II-1):

(II-1)

Example No. R² R³ R⁴ R⁵ R⁷ R⁹ m.p. (° C.) II-1-1 H Me Me Cl Cl CF₃ 185-186 II-1-2 H Me Me Cl Cl OCH₂CF₃ 207-208 II-1-3 H Me Me Cl Cl Cl 225-226 II-1-4 H Me Me Cl Cl Br 162-164 II-1-5 H Me Cl Cl Cl CF₃ 155-157 II-1-6 H Me Cl Cl Cl OCH₂CF₃ 192-195 II-1-7 H Me Cl Cl Cl Cl 205-206 II-1-8 H Me Cl Cl Cl Br 245-246 II-1-9 H i-Pr Me Cl Cl CF₃ 195-196 II-1-10 H i-Pr Me Cl Cl OCH₂CF₃ 217-218 II-1-11 H i-Pr Me Cl Cl Cl 173-175 II-1-12 H i-Pr Me Cl Cl Br 159-161 II-1-13 H i-Pr Cl Cl Cl CF₃ 200-201 II-1-14 H i-Pr Cl Cl Cl OCH₂CF₃ 232-235 II-1-15 H i-Pr Cl Cl Cl Cl 197-199 II-1-16 H i-Pr Cl Cl Cl Br 188-190 II-1-17 H Et Me Cl Cl CF₃ 163-164 II-1-18 H Et Me Cl Cl OCH₂CF₃ 205-207 II-1-19 H Et Me Cl Cl Cl 199-200 II-1-20 H Et Me Cl Cl Br 194-195 II-1-21 H Et Cl Cl Cl CF₃ 201-202 II-1-22 H Et Cl Cl Cl Cl 206-208 II-1-23 H Et Cl Cl Cl Br 214-215 II-1-24 H t-Bu Me Cl Cl CF₃ 223-225 II-1-25 H t-Bu Me Cl Cl Cl 163-165 II-1-26 H t-Bu Me Cl Cl Br 159-161 II-1-27 H t-Bu Cl Cl Cl CF₃ 170-172 II-1-28 H t-Bu Cl Cl Cl Cl 172-173 II-1-29 H t-Bu Cl Cl Cl Br 179-180 II-1-30 H Me Me Br Cl CF₃ 222-223 II-1-31 H Et Me Br Cl CF₃ 192-193 II-1-32 H i-Pr Me Br Cl CF₃ 197-198 II-1-33 H t-Bu Me Br Cl CF₃ 247-248 II-1-34 H Me Me Br Cl Cl 140-141 II-1-35 H Et Me Br Cl Cl 192-194 II-1-36 H i-Pr Me Br Cl Cl 152-153 II-1-37 H t-Bu Me Br Cl Cl 224-225 II-1-38 H Me Me Br Cl Br 147-149 II-1-39 H Et Me Br Cl Br 194-196 II-1-40 H i-Pr Me Br Cl Br 185-187 II-1-41 H t-Bu Me Br Cl Br 215-221 II-1-42 H Me Me I Cl CF₃ 199-200 II-1-43 H Et Me I Cl CF₃ 199-200 II-1-44 H i-Pr Me I Cl CF₃ 188-189 II-1-45 H t-Bu Me I Cl CF₃ 242-243 II-1-46 H Me Me I Cl Cl 233-234 II-1-47 H Et Me I Cl Cl 196-197 II-1-48 H i-Pr Me I Cl Cl 189-190 II-1-49 H t-Bu Me I Cl Cl 228-229 II-1-50 H Me Me I Cl Br 229-230 II-1-51 H iPr Me I Cl Br 191-192 II-1-52 H Me Br Br Cl CF₃ 162-163 II-1-53 H Et Br Br Cl CF₃ 188-189 II-1-54 H i-Pr Br Br Cl CF₃ 192-193 II-1-55 H t-Bu Br Br Cl CF₃ 246-247 II-1-56 H Me Br Br Cl Cl 188-190 II-1-57 H Et Br Br Cl Cl 192-194 II-1-58 H i-Pr Br Br Cl Cl 197-199 II-1-59 H t-Bu Br Br Cl C1 210-212 II-1-60 H Me Br Br Cl Br 166-168 II-1-61 H Et Br Br Cl Br 196-197 II-1-62 H i-Pr Br Br Cl Br 162-163 II-1-63 H t-Bu Br Br Cl Br 194-196 II-1-64 H t-Bu Cl Br Cl CF₃ 143-145 II-1-65 Me Me Br Br Cl Cl 153-155 II-1-66 Me Me Me Br Cl CF₃ 207-208 II-1-67 Me Me Cl Cl Cl Cl 231-232 II-1-68 Me Me Br Br Cl Br 189-190 II-1-69 Me Me Cl Cl Cl Br 216-218 II-1-70 Me Me Cl Cl Cl CF₃ 225-227 II-1-71 Me Me Br Br Cl CF₃ 228-229 II-1-72 H i-Pr Me H Cl CF₃ 237-239 and also an active compound of the formula (I) (group 1) or of group 2 selected from the compounds (2-1) to (2-7).

Especially preferred are active compound combinations comprising a compound of the following formulae

and also an active compound of the formula (I) (group 1) or of group 2 selected from the compounds (2-1) to (2-7).

Emphasis is given to active compound combinations comprising the compound of the formula (II-1-9) and the stated active compound of the formula (I) (group 1) or of group 2:

-   a) Active compound combinations comprising (II-1-9) and (I-a-4). -   b) Active compound combinations comprising (II-1-9) and (2-2)     buprofezin. -   c) Active compound combinations comprising (II-1-9) and (2-6)     flonicamid. -   d) Active compound combinations comprising (II-1-9) and (2-7)     pirimicarb.

Emphasis is given to the following specifically stated active compound combinations (2-component mixtures) comprising one compound of the formula (I) and one compound of the formula (II-1) or of group 2:

Active compound combination No. comprising 1a) (I-a-4) and (II-1-1) 1b) (2-2) buprofezin and (II-1-1) 1c) (2-6) flonicamid and (II-1-1) 1d) (2-7) pirimicarb and (II-1-1) 2a) (I-a-4) and (II-1-2) 2b) (2-2) buprofezin and (II-1-2) 2c) (2-6) flonicamid and (II-1-2) 2d) (2-7) pirimicarb and (II-1-2) 3a) (I-a-4) and (II-1-3) 3b) (2-2) buprofezin and (II-1-3) 3c) (2-6) flonicamid and (II-1-3) 3d) (2-7) pirimicarb and (II-1-3) 4a) (I-a-4) and (II-1-4) 4b) (2-2) buprofezin and (II-1-4) 4c) (2-6) flonicamid and (II-1-4) 4d) (2-7) pirimicarb and (II-1-4) 5a) (I-a-4) and (II-1-5) 5b) (2-2) buprofezin and (II-1-5) 5c) (2-6) flonicamid and (II-1-5) 5d) (2-7) pirimicarb and (II-1-5) 6a) (I-a-4) and (II-1-6) 6b) (2-2) buprofezin and (II-1-6) 6c) (2-6) flonicamid and (II-1-6) 6d) (2-7) pirimicarb and (II-1-6) 7a) (I-a-4) and (II-1-7) 7b) (2-2) buprofezin and (II-1-7) 7c) (2-6) flonicamid and (II-1-7) 7d) (2-7) pirimicarb and (II-1-7) 8a) (I-a-4) and (II-1-8) 8b) (2-2) buprofezin and (II-1-8) 8c) (2-6) flonicamid and (II-1-8) 8d) (2-7) pirimicarb and (II-1-8) 9a) (I-a-4) and (II-1-9) 9b) (2-2) buprofezin and (II-1-9) 9c) (2-6) flonicamid and (II-1-9) 9d) (2-7) pirimicarb and (II-1-9) 10a) (I-a-4) and (II-1-11) 10b) (2-2) buprofezin and (II-1-11) 10c) (2-6) flonicamid and (II-1-11) 10d) (2-7) pirimicarb and (II-1-11) 11a) (I-a-4) and (II-1-12) 11b) (2-2) buprofezin and (II-1-12) 11c) (2-6) flonicamid and (II-1-12) 11d) (2-7) pirimicarb and (II-1-12) 12a) (I-a-4) and (II-1-13) 12b) (2-2) buprofezin and (II-1-13) 12c) (2-6) flonicamid and (II-1-13) 12d) (2-7) pirimicarb and (II-1-13) 13a) (I-a-4) and (II-1-15) 13b) (2-2) buprofezin and (II-1-15) 13c) (2-6) flonicamid and (II-1-15) 13d) (2-7) pirimicarb and (II-1-15) 14a) (I-a-4) and (II-1-16) 14b) (2-2) buprofezin and (II-1-16) 14c) (2-6) flonicamid and (II-1-16) 14d) (2-7) pirimicarb and (II-1-16) 15a) (I-a-4) and (II-1-19) 15b) (2-2) buprofezin and (II-1-19) 15c) (2-6) flonicamid and (II-1-19) 15d) (2-7) pirimicarb and (II-1-19) 16a) (I-a-4) and (II-1-21) 16b) (2-2) buprofezin and (II-1-21) 16c) (2-6) flonicamid and (II-1-21) 16d) (2-7) pirimicarb and (II-1-21) 17a) (I-a-4) and (II-1-22) 17b) (2-2) buprofezin and (II-1-22) 17c) (2-6) flonicamid and (II-1-22) 17d) (2-7) pirimicarb and (II-1-22) 18a) (I-a-4) and (II-1-23) 18b) (2-2) buprofezin and (II-1-23) 18c) (2-6) flonicamid and (II-1-23) 18d) (2-7) pirimicarb and (II-1-23) 19a) (I-a-4) and (II-1-24) 19b) (2-2) buprofezin and (II-1-24) 19c) (2-6) flonicamid and (II-1-24) 19d) (2-7) pirimicarb and (II-1-24) 20a) (I-a-4) and (II-1-26) 20b) (2-2) buprofezin and (II-1-26) 20c) (2-6) flonicamid and (II-1-26) 20d) (2-7) pirimicarb and (II-1-26) 21a) (I-a-4) and (II-1-27) 21b) (2-2) buprofezin and (II-1-27) 21c) (2-6) flonicamid and (II-1-27) 21d) (2-7) pirimicarb and (II-1-27) 22a) (I-a-4) and (II-1-29) 22b) (2-2) buprofezin and (II-1-29) 22c) (2-6) flonicamid and (II-1-29) 22d) (2-7) pirimicarb and (II-1-29) 23a) (I-a-4) and (II-1-30) 23b) (2-2) buprofezin and (II-1-30) 23c) (2-6) flonicamid and (II-1-30) 23d) (2-7) pirimicarb and (II-1-30) 24a) (I-a-4) and (II-1-31) 24b) (2-2) buprofezin and (II-1-31) 24c) (2-6) flonicamid and (II-1-31) 24d) (2-7) pirimicarb and (II-1-31) 25a) (I-a-4) and (II-1-32) 25b) (2-2) buprofezin and (II-1-32) 25c) (2-6) flonicamid and (II-1-32) 25d) (2-7) pirimicarb and (II-1-32) 26a) (I-a-4) and (II-1-33) 26b) (2-2) buprofezin and (II-1-33) 26c) (2-6) flonicamid and (II-1-33) 26d) (2-7) pirimicarb and (II-1-33) 27a) (I-a-4) and (II-1-38) 27b) (2-2) buprofezin and (II-1-38) 27c) (2-6) flonicamid and (II-1-38) 27d) (2-7) pirimicarb and (II-1-38) 28a) (I-a-4) and (II-1-39) 28b) (2-2) buprofezin and (II-1-39) 28c) (2-6) flonicamid and (II-1-39) 28d) (2-7) pirimicarb and (II-1-39) 29a) (I-a-4) and (II-1-40) 29b) (2-2) buprofezin and (II-1-40) 29c) (2-6) flonicamid and (II-1-40) 29d) (2-7) pirimicarb and (II-1-40) 30a) (I-a-4) and (II-1-42) 30b) (2-2) buprofezin and (II-1-42) 30c) (2-6) flonicamid and (II-1-42) 30d) (2-7) pirimicarb and (II-1-42) 31a) (I-a-4) and (II-1-43) 31b) (2-2) buprofezin and (II-1-43) 31c) (2-6) flonicamid and (II-1-43) 31d) (2-7) pirimicarb and (II-1-43) 32a) (I-a-4) and (II-1-44) 32b) (2-2) buprofezin and (II-1-44) 32c) (2-6) flonicamid and (II-1-44) 32d) (2-7) pirimicarb and (II-1-44) 33a) (I-a-4) and (II-1-50) 33b) (2-2) buprofezin and (II-1-50) 33c) (2-6) flonicamid and (II-1-50) 33d) (2-7) pirimicarb and (II-1-50) 34a) (I-a-4) and (II-1-51) 34b) (2-2) buprofezin and (II-1-51) 34c) (2-6) flonicamid and (II-1-51) 34d) (2-7) pirimicarb and (II-1-51) 35a) (I-a-4) and (II-1-52) 35b) (2-2) buprofezin and (II-1-52) 35c) (2-6) flonicamid and (II-1-52) 35d) (2-7) pirimicarb and (II-1-52) 36a) (I-a-4) and (II-1-53) 36b) (2-2) buprofezin and (II-1-53) 36c) (2-6) flonicamid and (II-1-53) 36d) (2-7) pirimicarb and (II-1-53) 37a) (I-a-4) and (II-1-54) 37b) (2-2) buprofezin and (II-1-54) 37c) (2-6) flonicamid and (II-1-54) 37d) (2-7) pirimicarb and (II-1-54) 38a) (I-a-4) and (II-1-55) 38b) (2-2) buprofezin and (II-1-55) 38c) (2-6) flonicamid and (II-1-55) 38d) (2-7) pirimicarb and (II-1-55) 39a) (I-a-4) and (II-1-56) 39b) (2-2) buprofezin and (II-1-56) 39c) (2-6) flonicamid and (II-1-56) 39d) (2-7) pirimicarb and (II-1-56) 40a) (I-a-4) and (II-1-57) 40b) (2-2) buprofezin and (II-1-57) 40c) (2-6) flonicamid and (II-1-57) 40d) (2-7) pirimicarb and (II-1-57) 41a) (I-a-4) and (II-1-58) 41b) (2-2) buprofezin and (II-1-58) 41c) (2-6) flonicamid and (II-1-58) 41d) (2-7) pirimicarb and (II-1-58) 42a) (I-a-4) and (II-1-60) 42b) (2-2) buprofezin and (II-1-60) 42c) (2-6) flonicamid and (II-1-60) 42d) (2-7) pirimicarb and (II-1-60) 43a) (I-a-4) and (II-1-61) 43b) (2-2) buprofezin and (II-1-61) 43c) (2-6) flonicamid and (II-1-61) 43d) (2-7) pirimicarb and (II-1-61) 44a) (I-a-4) and (II-1-62) 44b) (2-2) buprofezin and (II-1-62) 44c) (2-6) flonicamid and (II-1-62) 44d) (2-7) pirimicarb and (II-1-62) 45a) (I-a-4) and (II-1-64) 45b) (2-2) buprofezin and (II-1-64) 45c) (2-6) flonicamid and (II-1-64) 45d) (2-7) pirimicarb and (II-1-64) 46a) (I-a-4) and (II-1-65) 46b) (2-2) buprofezin and (II-1-65) 46c) (2-6) flonicamid and (II-1-65) 46d) (2-7) pirimicarb and (II-1-65) 47a) (I-a-4) and (II-1-66) 47b) (2-2) buprofezin and (II-1-66) 47c) (2-6) flonicamid and (II-1-66) 47d) (2-7) pirimicarb and (II-1-66) 48a) (I-a-4) and (II-1-67) 48b) (2-2) buprofezin and (II-1-67) 48c) (2-6) flonicamid and (II-1-67) 48d) (2-7) pirimicarb and (II-1-67) 49a) (I-a-4) and (II-1-68) 49b) (2-2) buprofezin and (II-1-68) 49c) (2-6) flonicamid and (II-1-68) 49d) (2-7) pirimicarb and (II-1-68) 50a) (I-a-4) and (II-1-69) 50b) (2-2) buprofezin and (II-1-69) 50c) (2-6) flonicamid and (II-1-69) 50d) (2-7) pirimicarb and (II-1-69) 51a) (I-a-4) and (II-1-70) 51b) (2-2) buprofezin and (II-1-70) 51c) (2-6) flonicamid and (II-1-70) 51d) (2-7) pirimicarb and (II-1-70) 52a) (I-a-4) and (II-1-71) 52b) (2-2) buprofezin and (II-1-71) 52c) (2-6) flonicamid and (II-1-71) 52d) (2-7) pirimicarb and (II-1-71) 53a) (I-a-4) and (II-1-72) 53b) (2-2) buprofezin and (II-1-72) 53c) (2-6) flonicamid and (II-1-72) 53d) (2-7) pirimicarb and (II-1-72)

However, the general or preferred radical definitions or illustrations given above can also be combined with one another as desired, i.e. including combinations between the respective ranges and preferred ranges. They apply both to the end products and, correspondingly, to precursors and intermediates.

Preference according to the invention is given to active compound combinations comprising the compounds of the formula (I) or a compound of group 2 and also at least one compound of the formula (II) where the individual radicals are a combination of the meanings given above as being preferred (preferable).

Particular preference according to the invention is given to active compound combinations comprising the compounds of the formula (I) or a compound of group 2 and also at least one compound of the formula (II) where the individual radicals are a combination of the meanings given above as being particularly preferred.

Very particular preference according to the invention is given to active compound combinations comprising the compounds of the formula (I) or a compound of group 2 and also at least one compound of the formula (II) where the individual radicals are a combination of the meanings given above as being very particularly preferred.

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, can in each case be straight-chain or branched as far as this is possible, including in combination with heteroatoms, such as, for example, in alkoxy.

Optionally substituted radicals may be mono- or polysubstituted, where in the case of polysubstitution the substituents can be identical or different.

In addition, the active compound combinations may also comprise further fungicidally, acaricidally or insecticidally active co-components.

If the active compounds in the active compound combinations according to the invention are present in certain weight ratios, the synergistic effect is particularly pronounced. The mixing ratios required for finding the synergism are not necessarily the preferred mixing ratios relevant for 100% activity. However, the weight ratios of the active compounds in the active compound combinations can be varied within a relatively wide range. In general, the combinations according to the invention comprise active compounds of the formula (I) or a compound of group 2 and the mixing partner of the formula (II) in the stated preferred and particularly preferred mixing ratios:

The mixing ratios are based on weight ratios. The ratio is to be understood as meaning active compound of the formula (I): mixing partner

Preferred Particularly preferred Mixing partner mixing ratio mixing ratio (I-a-4) 10:1 to 1:10 5:1 to 1:5 Amitraz  5:1 to 1:20  1:1 to 1:10 Buprofezin 10:1 to 1:10 5:1 to 1:5 Pymetrozine 10:1 to 1:10 5:1 to 1:5 Pyriproxyphen 10:1 to 1:10 5:1 to 1:5 Triazamate 10:1 to 1:10 5:1 to 1:5 Flonicamid 10:1 to 1:10 5:1 to 1:5 Pirimicarb 10:1 to 1:10 5:1 to 1:5

The active compound combinations of the invention are suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, found in agriculture, in animal health, in forests, in gardens and leisure facilities, in the protection of stored products and materials and in the hygiene sector, while exhibiting good tolerability to plants, low toxicity to warm-blooded species and good environmental compatibility. They are active against normally sensitive and resistant species, and against all or individual developmental stages. The abovementioned pests include:

From the order of the Isopoda, for example, Oniscus asellus, Armadillidium vulgare, Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus, Scutigera spp.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.

From the order of the Blattaria, for example, Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Phthiraptera, for example, Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp.

From the order of the Thysanoptera, for example, Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella accidentalis.

From the order of the Heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.

From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria melloniella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cnaphalocerus spp., Oulema oryzae.

From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrofica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptus oryzophilus.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomyza spp.

From the order of the Siphonaptera, for example, Xenopsylla cheopis, Ceratophyllus spp.

From the class of the Arachnida, for example, Scorpio maurus, Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus spp.

The plant-parasitic nematodes include, for example, Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelenchus spp.

The active compound combinations of the invention of the compounds of the formula (I) and at least one compound 1 to 15 are particularly suitable for controlling “biting” pests. These include, in particular, the following pests:

From the order of the Lepidoptera for example, Pectinophora gossypiella, Bupalus piniiarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cnaphalocerus spp., Oulema oryzae.

From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus.

The active compound combinations of the invention of the compounds of the formula (I) and at least one compound 5 to 8 are additionally particularly suitable for controlling “sucking” pests. These include, in particular, the following pests:

From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.

The active compound combinations of the invention have, in particular, excellent activity against caterpillars, beetle larvae, spider mites, aphids and leaf-mining flies.

The active compound combinations of the invention can be converted into the customary formulations such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with active compound, and microencapsulations in polymeric materials.

These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is, liquid solvents and/or solid carriers, optionally with the use of surfactants, that is, emulsifiers and/or dispersants, and/or foam formers.

If the extender used is water, it is also possible, for example, to use organic solvents as cosolvents. The following are essentially suitable as liquid solvents: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example mineral oil fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, or else water.

Suitable solid carriers are: for example ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic materials such as finely divided silica, alumina and silicates; suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, or else protein hydrolysates; suitable dispersants are: for example lignin-sulfite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic colorants such as alizarin colorants, azo colorants and metal phthalocyanine colorants, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.

The active compound combinations of the invention can be present in their commercially available formulations and in the use forms, prepared from these formulations, as a mixture with other active compounds, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides. The insecticides include, for example, phosphates, carbamates, carboxylates, chlorinated hydrocarbons, phenylureas, and substances produced by microorganisms, inter alia.

Mixtures with other known active compounds such as herbicides or with fertilizers and growth regulators are also possible.

When used as insecticides, the active compound combinations of the invention can furthermore be present in their commercially available formulations and in the use forms, prepared from these formulations, as a mixture with synergists. Synergists are compounds which increase the action of the active compounds, without it being necessary for the synergist added to be active itself.

The active compound content of the use forms prepared from the commercially available formulations can vary within wide limits. The active compound concentration of the use forms can be from 0.0000001 to 95% by weight of active compound, preferably between 0.0001 and 1% by weight.

The compounds are employed in a customary manner appropriate for the use forms.

When used against hygiene pests and stored-product pests, the active compound combinations are distinguished by an excellent residual action on wood and clay as well as good stability to alkali on limed substrates.

The active compound combinations of the invention are not only active against plant pests, hygiene pests and stored-product pests, but also, in the veterinary medicine sector, against animal parasites (ectoparasites) such as hard ticks, soft ticks, mange mites, harvest mites, flies (stinging and licking), parasitizing fly larvae, lice, head lice, bird lice and fleas. These parasites include:

From the order of the Anoplurida, for example, Haematopinus spp., Linognathus spp., Pedicuius spp., Phtirus spp., Solenopotes spp.

From the order of the Mallophagida and the suborders Amblycerina and Ischnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.

From the order Diptera and the suborders Nematocerina and Brachycerina, for example, Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp.; Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.

From the order of the Siphonapterida, for example, Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.

From the order of the Heteropterida, for example, Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.

From the order of the Blattarida, for example, Blatta orientalis, Periplaneta americana, Blattella germanica, Supella spp.

From the subclass of the Acaria (Acarida) and the orders of the Meta- and Mesostigmata, for example, Argas spp., Ornithodonis spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp.

From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata), for example, Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.

The active compound combinations of the invention are also suitable for controlling arthropods which attack agricultural livestock such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, honey-bees, other domestic animals such as, for example, dogs, cats, caged birds, aquarium fish and so-called experimental animals such as, for example, hamsters, guinea pigs, rats and mice. By controlling these arthropods, cases of death and reductions in productivity (for meat, milk, wool, hides, eggs, honey and the like) should be diminished, so that more economical and simpler animal husbandry is possible by the use of the active compound combinations of the invention.

The active compound combinations of the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, potions, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration such as, for example, by injections (intramuscularly, subcutaneously, intravenously, intraperitoneally and the like), implants, by nasal administration, by dermal administration in the form of, for example, immersing or dipping, spraying, pouring-on, spotting-on, washing, dusting, and with the aid of active-compound-comprising molded articles such as collars, ear tags, tail tags, limb bands, halters, marking devices and the like.

When used for cattle, poultry, domestic animals and the like, the active compound combinations can be applied as formulations (for example powders, emulsions, flowables) comprising the active compounds in an amount of 1 to 80% by weight, either directly or after 100- to 10,000-fold dilution, or they may be used as a chemical dip.

Moreover, it has been found that the active compound combinations of the invention show a potent insecticidal action against insects which destroy industrial materials.

The following insects may be mentioned by way of example and with preference, but not by way of limitation:

Beetles such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Emobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spec., Tryptodendron spec., Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec., Dinoderus minutus.

Dermapterans such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.

Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.

Bristle-tails such as Lepisma saccharina.

Industrial materials in the present context are understood as meaning non-living materials such as, preferably, polymers, adhesives, glues, paper and board, leather, wood, timber products and paints.

The material which is to be protected from insect attack is very particularly preferably wood and timber products.

Wood and timber products which can be protected by the composition of the invention, or mixtures comprising it, are to be understood as meaning, for example:

Construction timber, wooden beams, railway sleepers, bridge components, jetties, vehicles made of wood, boxes, pallets, containers, telephone poles, wood lagging, windows and doors made of wood, plywood, chipboard, joinery, or timber products which quite generally are used in house construction or building joinery.

The active compound combinations can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or pastes.

The abovementioned formulations can be prepared in a manner known per se, for example by mixing the active compounds with at least one solvent or diluent, emulsifier, dispersant and/or binder or fixative, water repellant, if desired desiccants and UV stabilizers, and if desired colorants and pigments and other processing auxiliaries.

The insecticidal compositions or concentrates used for protecting wood and timber products comprise the active compound of the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight

The amount of composition or concentrate employed depends on the species and the abundance of the insects and on the medium. The optimal quantity to be employed can be determined in each case by test series upon application. In general, however, it will suffice to employ 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active compound, based on the material to be protected.

A suitable solvent and/or diluent is an organochemical solvent or solvent mixture and/or an oily or oil-type organochemical solvent or solvent mixture of low volatility and/or a polar organochemical solvent or solvent mixture and/or water and, if appropriate, an emulsifier and/or wetter.

Organochemical solvents which are preferably employed are oily or oil-type solvents with an evaporation number of above 35 and a flash point of above 30° C., preferably above 45° C. Such oily and oil-type solvents which are insoluble in water and of low volatility and which are used are suitable mineral oils or their aromatic fractions or mineral-oil-containing solvent mixtures, preferably white spirit, petroleum and/or alkylbenzene.

Mineral oils with a boiling range of 170 to 220° C., white spirit with a boiling range of 170 to 220° C., spindle oil with a boiling range of 250 to 350° C., petroleum and aromatics with a boiling range of 160 to 280° C., oil of turpentine, and the like are advantageously used.

In a preferred embodiment, liquid aliphatic hydrocarbons with a boiling range of 180 to 210° C. or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range of 180 to 220° C. and/or spindle oil and/or monochloronaphthalene, preferably α-monochloronaphthalene, are used.

The organic oily or oil-type solvents of low volatility and with an evaporation number of above 35 and a flash point of above 30° C., preferably above 45° C., can be replaced in part by organochemical solvents of high or medium volatility, with the proviso that the solvent mixture also has an evaporation number of above 35 and a flash point of above 30° C., preferably above 45° C., and that the mixture is soluble or emulsifiable in this solvent mixture.

In a preferred embodiment, some of the organochemical solvent or solvent mixture or an aliphatic polar organochemical solvent or solvent mixture is replaced. Aliphatic organochemical solvents which contain hydroxyl and/or ester and/or ether groups are preferably used, such as, for example, glycol ethers, esters or the like.

Organochemical binders used for the purposes of the present invention are the synthetic resins and/or binding drying oils which are known per se and which can be diluted in water and/or dissolved or dispersed or emulsified in the organochemical solvents employed, in particular binders composed of, or comprising, an acrylate resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenol resin, hydrocarbon resin such as indene/coumarone resin, silicone resin, drying vegetable and/or drying oils and/or physically drying binders based on a natural and/or synthetic resin.

The synthetic resin employed as binder can be employed in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances may also be used as binders, in amounts of up to 10% by weight. In addition, colorants, pigments, water repellants, odor-masking agents, and inhibitors or anticorrosive agents and the like, all of which are known per se, can be employed.

In accordance with the invention, the composition or the concentrate preferably comprises, as organochemical binders, at least one alkyd resin or modified alkyd resin and/or a drying vegetable oil. Alkyd resins which are preferably used in accordance with the invention are those with an oil content of over 45% by weight, preferably 50 to 68% by weight.

Some or all of the abovementioned binder can be replaced by a fixative (mixture) or plasticizer (mixture). These additives are intended to prevent volatilization of the active compounds, and also crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on 100% of binder employed).

The plasticizers are from the chemical classes of the phthalic esters, such as dibutyl phthalate, dioctyl phthalate or benzyl butyl phthalate, phosphoric esters such as tributyl phosphate, adipic esters such as di(2-ethylhexyl)adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, glycerol ethers or higher-molecular-weight glycol ethers, glycerol esters and p-toluenesulfonic esters.

Fixatives are based chemically on polyvinyl alkyl ethers such as, for example, polyvinyl methyl ether, or ketones such as benzophenone and ethylenebenzophenone.

Other suitable solvents or diluents are, in particular, water, if appropriate as a mixture with one or more of the abovementioned organochemical solvents or diluents, emulsifiers and dispersants.

Particularly effective timber protection is achieved by industrial-scale impregnating processes, for example the vacuum, double-vacuum or pressure processes.

The active compound combinations of the invention can at the same time be employed for protecting objects which come into contact with saltwater or brackish water, such as hulls, screens, nets, buildings, moorings and signaling systems, against fouling.

Fouling by sessile Oligochaeta, such as Serpulidae, and by shells and species from the Ledamorpha group (goose barnacles), such as various Lepas and Scalpellum species, or by species from the Balanomorpha group (acorn barnacles), such as Balanus or Pollicipes species, increases the frictional drag of ships and, as a consequence, leads to a marked increase in operation costs owing to higher energy consumption and additionally frequent stops in the dry dock.

Apart from fouling by algae, for example Ectocarpus sp. and Ceramium sp., fouling by sessile Entomostraka groups, which come under the generic term Cirripedia (cirriped crustaceans), is of particular importance.

Surprisingly, it has now been found that the active compound combinations of the invention have an outstanding antifouling action.

Using the active compound combinations of the invention allows the use of heavy metals such as, for example, in bis(trialkyltin) sulfides, tri-n-butyltin laurate, tri-n-butyltin chloride, copper(I) oxide, triethyltin chloride, tri-n-butyl(2-phenyl-4-chlorophenoxy)tin, tributyltin oxide, molybdenum disulfide, antimony oxide, polymeric butyl titanate, phenyl(bispyridine)bismuth chloride, tri-n-butyltin fluoride, manganese ethylenebisthiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisthiocarbamate, zinc salts and copper salts of 2-pyridinethiol 1-oxide, bisdimethyldithiocarbamoylzinc ethylenebisthiocarbamate, zinc oxide, copper(I) ethylene-bisdithiocarbamate, copper thiocyanate, copper naphthenate and tributyltin halides to be dispensed with, or the concentration of these compounds to be substantially reduced.

If appropriate, the ready-to-use antifouling paints can additionally comprise other active compounds, preferably algicides, fungicides, herbicides, molluscicides, or other antifouling active compounds.

Preferable suitable components in combination with the antifouling compositions according to the invention are:

algicides such as 2-tert-butylamino-4-cyclopropylamino-6-methylthio-1,3,5-triazine, dichlorophen, diuron, endothal, fentin acetate, isoproturon, methabenzthiazuron, oxyfluorfen, quinoclamine and terbutryn;

fungicides such as benzo[b]thiophenecarboxylic acid cyclohexylamide S,S-dioxide, dichlofluanid, fluorfolpet, 3-iodo-2-propinyl butylcarbamate, tolylfluanid and azoles such as azaconazole, cyproconazole, epoxyconazole, hexaconazole, metconazole, propiconazole and tebuconazole; molluscicides such as fentin acetate, metaldehyde, methiocarb, niclosamid, thiodicarb and trimethacarb; or conventional antifouling active compounds such as 4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethylparatryl sulfone, 2-(N,N-dimethylthiocarbamoylthio)-5-nitrothiazyl, potassium, copper, sodium and zinc salts of 2-pyridinethiol 1-oxide, pyridine/triphenylborane, tetrabutyldistannoxane, 2,3,5,6-tetrachloro-4-methylsulfonyl)pyridine, 2,4,5,6-tetrachloroisophthalonitrile, tetramethylthiuram disulfide and 2,4,6-trichlorophenylmaleimide.

The antifouling compositions used comprise the active compound combinations of the invention in a concentration of 0.001 to 50% by weight, in particular 0.01 to 20% by weight.

Moreover, the antifouling compositions of the invention comprise the customary components such as, for example, those described in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 1973.

Besides the algicidal, fungicidal, molluscicidal active compounds and insecticidal active compounds of the invention, antifouling paints comprise, in particular, binders.

Examples of recognized binders are polyvinyl chloride in a solvent system, chlorinated rubber in a solvent system, acrylic resins in a solvent system, in particular in an aqueous system, vinyl chloride/vinyl acetate copolymer systems in the form of aqueous dispersions or in the form of organic solvent systems, butadiene/styrene/acrylonitrile rubbers, drying oils such as linseed oil, resin esters or modified hardened resins in combination with tar or bitumens, asphalt and epoxy compounds, small amounts of chlorine rubber, chlorinated polypropylene and vinyl resins.

If appropriate, paints also comprise inorganic pigments, organic pigments or colorants which are preferably insoluble in salt water. Paints may furthermore comprise materials such as colophonium to allow controlled release of the active compounds. Furthermore, the paints may comprise plasticizers, modifiers which affect the rheological properties and other conventional constituents. The compounds of the invention or the abovementioned mixtures may also be incorporated into self-polishing antifouling systems.

The active compound combinations are also suitable for controlling animal pests, in particular insects, arachnids and mites, which are found in enclosed spaces such as, for example, dwellings, factory halls, offices, vehicle cabins and the like. They can be employed in domestic insecticide products for controlling these pests. They are active against sensitive and resistant species and against all developmental stages. These pests include:

From the order of the Scorpionidea, for example, Buthus occitanus.

From the order of the Acarina, for example, Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.

From the order of the Araneae, for example, Aviculariidae, Araneidae.

From the order of the Opiliones, for example, Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.

From the order of the Isopoda, for example, Oniscus asellus, Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus, Polydesmus spp.

From the order of the Chilopoda, for example, Geophilus spp.

From the order of the Zygentoma, for example, Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.

From the order of the Blattaria, for example, Blatta orientalies, Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.

From the order of the Saltatoria, for example, Acheta domesticus.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Kalotermes spp., Reticulitermes spp.

From the order of the Psocoptera, for example, Lepinatus spp., Liposcelis spp.

From the order of the Coleptera, for example, Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum.

From the order of the Diptera, for example, Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp., Stomoxys calcitrans, Tipula paludosa.

From the order of the Lepidoptera, for example, Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.

From the order of the Siphonaptera, for example, Ctenocephalides canis, Ctenocephalides filis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.

From the order of the Hymenoptera, for example, Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.

From the order of the Anoplura, for example, Pediculus humanus capitis, Pediculus humanus corporis, Phthirus pubis.

From the order of the Heteroptera, for example, Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.

They are used as aerosols, pressureless spray products, for example pump and atomizer sprays, automatic fogging systems, foggers, foams, gels, evaporator products with evaporator tablets made of cellulose or polymer, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-free, or passive, evaporation systems, moth papers, moth bags and moth gels, as granules or dusts, in baits for spreading or in bait stations.

According to the invention, it is possible to treat all plants and parts of plants. Plants are to be understood here as meaning all plants and plant populations such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' certificates. Parts of plants are to be understood as meaning all above-ground and below-ground parts and organs of plants, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stems, trunks, flowers, fruit-bodies, fruits and seeds and also roots, tubers and rhizomes. Parts of plants also include harvested plants and vegetative and generative propagation material, for example seedlings, tubers, rhizomes, cuttings and seeds.

The treatment of the invention of the plants and parts of plants with the active compounds is carried out directly or by action on their environment, habitat or storage area according to customary treatment methods, for example by dipping, spraying, evaporating, atomizing, broadcasting, brushing-on and, in the case of propagation material, in particular in the case of seeds, furthermore by one- or multi-layer coating.

As already mentioned above, it is possible to treat all plants and their parts according to the invention. In a preferred embodiment, wild plant species and plant cultivars, or those obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and parts thereof, are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The terms “parts”, “parts of plants” and “plant parts” have been explained above.

Particularly preferably, plants of the plant cultivars which are in each case commercially available or in use are treated according to the invention.

Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment of the invention may also result in superadditive (“synergistic”) effects. Thus, for example, reduced application rates and/or a widening of the activity spectrum and/or an increase in the activity of the substances and compositions which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, better quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products are possible which exceed the effects which were actually to be expected.

The transgenic plants or plant cultivars (i.e. those obtained by genetic engineering) which are preferred and to be treated according to the invention include all plants which, in the genetic modification, received genetic material which imparts particularly advantageous useful traits to these plants. Examples of such traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, better quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products. Further and particularly emphasized examples of such traits are a better defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and/or viruses, and also increased tolerance of the plants to certain herbicidally active compounds. Examples of transgenic plants which may be mentioned are the important crop plants, such as cereals (wheat, rice), maize, soya beans, potatoes, cotton, tobacco, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), and particular emphasis is given to maize, soya beans, potatoes, cotton, tobacco and oilseed rape. Traits that are particularly emphasized are the increased defense of the plants against insects, arachnids, nematodes and worms by toxins formed in the plants, in particular those formed in the plants by the genetic material from Bacillus thuringiensis (for example by the genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF and also combinations thereof) (hereinbelow referred to as “Bt plants”). Traits that are also particularly emphasized are the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and also resistance genes and correspondingly expressed proteins and toxins. Traits that are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulphonylureas, glyphosate or phosphinotricin (for example the “PAT” gene). The genes in question which impart the desired traits can also be present in combination with one another in the transgenic plants. Examples of “Bt plants”. which may be mentioned are maize varieties, cotton varieties, soya bean varieties and potato varieties which are sold under the trade names YIELD GARD® (for example maize, cotton, soya beans), KnockOut® (for example maize), StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants which may be mentioned are maize varieties, cotton varieties and soya bean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate, for example maize, cotton, soya beans), Liberty Link® (tolerance to phosphinotricin, for example oilseed rape), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulfonylureas, for example maize). Herbicide-resistant plants (plants bred in a conventional manner for herbicide tolerance) which may be mentioned include the varieties sold under the name Clearfield® (for example maize). Of course, these statements also apply to plant cultivars having these or still-to-be developed genetic traits, which plants will be developed and/or marketed in the future.

The plants listed can be treated according to the invention in a particularly advantageous manner with the active compound mixtures of the invention. The preferred ranges stated above for the mixtures also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the mixtures specifically mentioned in the present text.

The good insecticidal and acaricidal action of the active compound combinations of the invention can be seen from the examples which follow. While the individual active compounds show weaknesses in their action, the combinations show an action which exceeds a simple sum of actions.

A synergistic effect in insecticides and acaricides is always present when the action of the active compound combinations exceeds the total of the actions of the active compounds when applied individually.

The expected action for a given combination of two active compounds can be calculated as follows, using “Colby's formula” (cf. S. R. Colby, “Calculating Synergistic and Antagonistic Responses of Herbicide Combinations”, Weeds 1967, 15, 20-22):

If

-   X is the kill rate, expressed as a percentage of the untreated     control, when employing active compound A at an application rate of     m g/ha or in a concentration of m ppm, -   Y is the kill rate, expressed as a percentage of the untreated     control, when employing active compound B at an application rate of     n g/ha or in a concentration of n ppm and -   E is the kill rate, expressed as a percentage of the untreated     control, when employing active compounds A and B at application     rates of m and n g/ha or in a concentration of m and n ppm,     then

$E = {X + Y - \frac{X \cdot Y}{100}}$

If the actual insecticidal kill rate exceeds the calculated value, the action of the combination is superadditive, i.e. a synergistic effect is present. In this case, the actually observed kill rate must exceed the value calculated using the above formula for the expected kill rate (E).

USE EXAMPLES Example A

Aphis gossypii test Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.

Cotton leaves (Gossypium hirsutum) which are heavily infested by the cotton aphid (Aphis gossypii) are treated by being dipped into the preparation of active compound of the desired concentration.

After the desired period of time; the kill in % is determined. 100% means that all aphids have been killed; 0% means that none of the aphids have been killed. The determined kill rates are entered into Colby's formula (see page 41).

In this test, for example, the following active compound combination in accordance with the present application shows a synergistically enhanced activity compared to the active compounds applied on their own:

TABLE A1 Plant-damaging insects Aphis gossypii test Kill rate in % Concentration of active after 7^(d) Active compounds compound in ppm found* calc.**

 4 20

20 0 (II-1-9) + (2-2)buprofezin(1:5) 4 + 20 40 20 *found = activity found **calc. = activity calculated using Colby's formula

TABLE A2 Plant-damaging inserts Aphis gossypii test Kill rate in % Concentration of active after 6^(d) Active compounds compound in ppm found* calc.**

20 55

20 40 (II-1-9) + (2-6)flonicamid(1:1) 20 + 20 99 73 *found = activity found **calc. = activity calculated using Colby's formula

Example B

Myzus persicae test Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.

Cabbage leaves (Brassica oleracea) which are heavily infested by the green peach aphid (Myzus persicae) are treated by being dipped into the preparation of active compound of the desired concentration.

After the desired period of time, the kill in % is determined. 100% means that all aphids have been killed; 0% means that none of the aphids have been killed. The determined kill rates are entered into Colby's formula (see on page 41).

In this test, for example, the following active compound combination in accordance with the present application shows a synergistically enhanced activity compared to the active compounds applied on their own:

TABLE B1 Plant-damaging insects Myzus persicae test Kill rate in % Concentration of active after 6^(d) Active compounds compound in ppm found* calc.**

4 30

4 80 (II-1-9) + (I-a-4) (1:1) 4 + 4 98 86 *found = activity found **calc. = activity calculated using Colby's formula

TABLE B2 Plant-damaging insects Myzus persicae test Kill rate in % Concentration of active after 6^(d) Active compounds compound in ppm found* calc.**

4 0

4 40 (II-1-9) + (2-6)flonicamid(1:1) 4 + 4 95 40 *found = activity found **calc. = activity calculated using Colby's formula

Example C

Phaedon cochleariae larvae test Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and are populated with larvae of the mustard beetle (Phaedon cochleariae) while the leaves are still moist.

After the desired period of time, the kill in % is determined. 100% means that all beetle larvae have been killed; 0% means that none of the beetle larvae have been killed. The determined kill rates are entered into Colby's formula (see page 41).

In this test, for example, the following active compound combination in accordance with the present application shows a synergistically enhanced activity compared to the active compounds applied on their own:

TABLE C1 Plant-damaging insects Phaedon cochleariae larvae test Kill rate in % Concentration of active after 3^(d) Active compounds compound in ppm found* calc.**

0.16 5

100 20 (II-1-9) + (2-2) buprofezin (1:625) 0.16 + 100 65 24 *found = activity found **calc. = activity calculated using Colby's formula

TABLE C2 Plant-damaging insects Phaedon cochleariae larvae test Kill rate in % Concentration of active after 6^(d) Active compounds compound in ppm found* calc.**

0.16 0

4 15 (II-1-9) + (I-a-4) (1:25) 0.16 + 4 55 15 *found = activity found **calc. = activity calculated using Colby's formula

Example D

Plutella xylostella test (resistant strain) Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and are populated with caterpillars of the diamondback moth (Plutella xylostella, resistant strain) while the leaves are still moist.

After the desired period of time, the kill in % is determined. 100% means that all caterpillars have been killed; 0% means that none of the caterpillars have been killed. The determined kill rates are entered into Colby's formula (see page 41).

In this test, for example, the following active compound combination in accordance with the present application shows a synergistically enhanced activity compared to the active compounds applied on their own:

TABLE D Plant-damaging insects Plutella xylostella test (resistant strain) Kill rate in % Concentration of active after 6^(d) Active compounds compound in ppm found* calc.**

0.0064 0

0.16 0 (II-1-9) + (I-a-4) (1:25) 0.0064 + 0.16 65 0 *found = activity found **calc. = activity calculated using Colby's formula

Example E

Spodoptera frugiperda test Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and are populated with caterpillars of the army worm (Spodoptera frugiperda) while the leaves are still moist.

After the desired period of time, the kill in % is determined. 100% means that all caterpillars have been killed; 0% means that none of the caterpillars have been killed. The determined kill rates are entered into Colby's formula (see page 41).

In this test, for example, the following active compound combination in accordance with the present application shows a synergistically enhanced activity compared to the active compounds applied on their own:

TABLE E Plant-damaging insects Spodoptera frugiperda test Kill rate in % after Concentration of active 3^(d) Active compounds compound in ppm found* calc.**

0.16 45

100 5 (II-1-9) + (2-6) flonicamid (1:625) 0.16 + 100 100 47.75 *found = activity found **calc. = activity calculated using Colby's formula 

The invention claimed is:
 1. A composition for controlling animal pests comprising a synergistically effective active compound combination of the compound of the formula (I-a-4)

or at least one insecticidally active compound (group 2) selected from (2-2) buprofezin, (2-6) flonicamid, (2-7) pirimicarb, and at least one active compound from the group of the anthranilamides of the formula (II-1)

in which R² represents hydrogen or methyl, R³ represents C₁-C₄ alkyl, R⁴ represents methyl, trifluoromethyl, trifluoromethoxy, fluorine, chlorine, bromine or iodine, R⁵ represents hydrogen, fluorine, chlorine, bromine, iodine, trifluoromethyl or trifluoromethoxy, R⁷ represents chlorine or bromine, and R⁹ represents trifluoromethyl, chlorine, bromine, difluoromethoxy or trifluoroethoxy, wherein the weight ratio of the compound of formula (I-a-4) or the at least one insecticidally active compound (group 2) to the at least one active compound from the group of the anthranilamides is from 10:1 to 1:10.
 2. The composition as claimed in claim 1, comprising a synergistically effective active compound combination of the compound of the formula (I-a-4), and at least one compound from the group of the anthranilamides of the formula (II-1).
 3. The composition as claimed in claim 1, comprising a synergistically effective active compound combination of the compound pirimicarb, and at least one compound from the group of the anthranilamides of the formula (II-1).
 4. A process for preparing a pesticide, comprising mixing the synergistically effective active compound combination as defined in claim 1 with substances selected from the group consisting of extenders, surfactants and mixtures thereof.
 5. The composition as claimed in claim 1, wherein said weight ratio is from 5:1 to 1:5.
 6. The composition as claimed in claim 1, comprising a synergistically effective active compound combination of the compound (2-2) buprofezin and the compound of the formula (II-1-9)


7. The composition as claimed in claim 6, wherein the weight ratio of the compound (2-2) buprofezin and the compound of the formula (II-1-9) is 5:1.
 8. The composition as claimed in claim 6, comprising a synergistically effective active compound combination of the compound (2-6) flonicamid and the compound of the formula (II-1-9).
 9. The composition as claimed in claim 8, wherein the weight ratio of the compound (2-6) flonicamid and the compound of the formula (II-1-9) is 1:1.
 10. The composition as claimed in claim 2, wherein said compound from the group of the anthranilamides of the formula (II-1) is the compound of the formula (II-1-9)


11. The composition as claimed in claim 10, wherein the weight ratio of the compound of the formula (I-a-4) and the compound of the formula (II-1-9) is 1:1.
 12. The composition as claimed in claim 1, comprising a synergistically effective active compound combination of the compound (2-2) buprofezin and the compound of the formula (II-1-4)


13. The composition as claimed in claim 1, comprising a synergistically effective active compound combination of the compound (2-6) flonicamid and the compound of the formula (II-1-4)


14. The composition as claimed in claim 2, wherein said compound from the group of the anthranilamides of the formula (II-1) is the compound of the formula (II-1-4) 